#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/63/1506353.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1506353
loop_
_publ_author_name
'Deng, Bo-Liang'
'Hartman, Tracy L.'
'Buckheit, Jr, Robert W'
'Pannecouque, Christophe'
'De Clercq, Erik'
'Fanwick, Phillip E.'
'Cushman, Mark'
_publ_section_title
;
 Synthesis, anti-HIV activity, and metabolic stability of new
 alkenyldiarylmethane HIV-1 non-nucleoside reverse transcriptase
 inhibitors.
;
_journal_issue                   19
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              6140
_journal_page_last               6155
_journal_paper_doi               10.1021/jm050452s
_journal_volume                  48
_journal_year                    2005
_chemical_formula_moiety         'C23 H21 F4 N1 O4'
_chemical_formula_sum            'C23 H21 F4 N O4'
_chemical_formula_weight         451.42
_chemical_name_systematic        ' ?'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_type_scat_source
'International Tables for Crystallography (Vol C)'
_cell_angle_alpha                76.306(4)
_cell_angle_beta                 72.480(6)
_cell_angle_gamma                89.873(5)
_cell_formula_units_Z            2
_cell_length_a                   8.8822(7)
_cell_length_b                   9.7444(9)
_cell_length_c                   12.9675(17)
_cell_measurement_reflns_used    12884
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      2
_cell_volume                     1036.98(19)
_computing_cell_refinement       DENZO/SCALEPACK_(Otwinowski,_1996)
_computing_data_collection       Collect_(Nonius,_1998)
_computing_data_reduction        DENZO/SCALEPACK_(Otwinowski,_1996)
_computing_molecular_graphics
;
    ORTEP (Johnson, 1976)
    PLATON (Spek, 1997)
;
_computing_structure_refinement  SHELX97_(Sheldrick,_1997)
_computing_structure_solution    Direct_methods_(SIR2002,_Burla_et_al.,_2003)
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.9920
_diffrn_measured_fraction_theta_max 0.9830
_diffrn_measurement_device_type  Nonius_KappaCCD
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'graphite 002'
_diffrn_radiation_type           MO-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12884
_diffrn_reflns_theta_full        26.7
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_correction_T_min  0.9397
_exptl_absorpt_correction_type   multi-scan_(Otwinowski_&_Minor,_1997
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.45
_exptl_crystal_description       needle
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4879
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.068
_refine_ls_R_factor_gt           0.046
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'1/[σ²(Fo²)+(0.0722P)²+0.0000P] where P=(Fo²+2Fc²)/3  '
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.117
_refine_ls_wR_factor_ref         0.128
_reflns_number_gt                3461
_reflns_number_total             4884
_reflns_threshold_expression     >2.0σ(I)
_cod_data_source_file            jm050452ssi20050511_101711.cif
_cod_data_source_block           D360B
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc ' changed to 'calc'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_formula_sum        'C23 H21 F4 N1 O4'
_cod_database_code               1506353
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F(15) F 0.51248(11) 0.43740(9) 0.60528(8) 0.0314(2) Uani 1 1 d .
F(131) F 0.82823(12) 0.90036(12) 0.42973(8) 0.0436(3) Uani 1 1 d .
F(132) F 0.86049(15) 0.92048(17) 0.58102(10) 0.0734(5) Uani 1 1 d .
F(133) F 0.69223(16) 1.03845(12) 0.51987(13) 0.0782(5) Uani 1 1 d .
O(1) O 0.45837(12) 0.88842(11) 1.19260(9) 0.0256(3) Uani 1 1 d .
O(3) O 0.76606(12) 0.70803(12) 1.05674(10) 0.0303(3) Uani 1 1 d .
O(105) O 0.04900(14) 0.38066(14) 0.67673(11) 0.0394(3) Uani 1 1 d .
O(106) O -0.18222(14) 0.39441(13) 0.63986(11) 0.0371(3) Uani 1 1 d .
N(2) N 0.60442(15) 0.82415(14) 1.17674(12) 0.0280(3) Uani 1 1 d .
C(3) C 0.64116(17) 0.76428(16) 1.08837(13) 0.0238(3) Uani 1 1 d .
C(4) C 0.50460(16) 0.78313(15) 1.04719(12) 0.0221(3) Uani 1 1 d .
C(5) C 0.46690(17) 0.74141(15) 0.96162(12) 0.0229(3) Uani 1 1 d .
C(6) C 0.32276(17) 0.77726(15) 0.94379(12) 0.0224(3) Uani 1 1 d .
C(7) C 0.22418(17) 0.85756(16) 1.01120(13) 0.0237(3) Uani 1 1 d .
C(8) C 0.25808(17) 0.89972(15) 1.09699(13) 0.0233(3) Uani 1 1 d .
C(9) C 0.40152(17) 0.85825(15) 1.11211(12) 0.0215(3) Uani 1 1 d .
C(10) C 0.27149(17) 0.73036(15) 0.85736(12) 0.0226(3) Uani 1 1 d .
C(11) C 0.39796(17) 0.70636(15) 0.75840(12) 0.0225(3) Uani 1 1 d .
C(12) C 0.51499(17) 0.81370(16) 0.69314(13) 0.0243(3) Uani 1 1 d .
C(13) C 0.62746(17) 0.79444(16) 0.59767(12) 0.0235(3) Uani 1 1 d .
C(14) C 0.62852(17) 0.66814(16) 0.56538(13) 0.0247(3) Uani 1 1 d .
C(15) C 0.51356(18) 0.56305(16) 0.63314(13) 0.0246(3) Uani 1 1 d .
C(16) C 0.39964(17) 0.57834(16) 0.72808(13) 0.0240(3) Uani 1 1 d .
C(21) C 0.69459(19) 0.84905(17) 1.24650(14) 0.0305(4) Uani 1 1 d .
C(81) C 0.15168(18) 0.98569(17) 1.16770(14) 0.0286(4) Uani 1 1 d .
C(101) C 0.11752(17) 0.70935(16) 0.86899(13) 0.0247(3) Uani 1 1 d .
C(102) C 0.04215(18) 0.66627(16) 0.79168(13) 0.0255(3) Uani 1 1 d .
C(103) C -0.06418(19) 0.52914(17) 0.85065(14) 0.0281(4) Uani 1 1 d .
C(104) C -0.16553(18) 0.49145(17) 0.78391(14) 0.0286(4) Uani 1 1 d .
C(105) C -0.08388(18) 0.41699(16) 0.69601(14) 0.0268(3) Uani 1 1 d .
C(107) C -0.1239(2) 0.3187(2) 0.55430(16) 0.0422(5) Uani 1 1 d .
C(131) C 0.75104(19) 0.91267(18) 0.53144(14) 0.0324(4) Uani 1 1 d .
H(5) H 0.5375 0.6899 0.9166 0.027 Uiso 1 1 calc R
H(7) H 0.1283 0.8843 0.9966 0.028 Uiso 1 1 calc R
H(12) H 0.5178 0.9005 0.7141 0.029 Uiso 1 1 calc R
H(14) H 0.7047 0.6548 0.4998 0.030 Uiso 1 1 calc R
H(16) H 0.3232 0.5025 0.7723 0.029 Uiso 1 1 calc R
H(101) H 0.0461 0.7239 0.9359 0.030 Uiso 1 1 calc R
H(10A) H 0.1254 0.6518 0.7254 0.031 Uiso 1 1 calc R
H(10B) H -0.0217 0.7426 0.7660 0.031 Uiso 1 1 calc R
H(10C) H 0.0031 0.4504 0.8654 0.034 Uiso 1 1 calc R
H(10D) H -0.1344 0.5390 0.9236 0.034 Uiso 1 1 calc R
H(10E) H -0.2594 0.4305 0.8364 0.034 Uiso 1 1 calc R
H(10F) H -0.2039 0.5797 0.7477 0.034 Uiso 1 1 calc R
H(10G) H -0.0185 0.3602 0.5061 0.063 Uiso 1 1 calc R
H(10H) H -0.1962 0.3255 0.5095 0.063 Uiso 1 1 calc R
H(10I) H -0.1174 0.2189 0.5892 0.063 Uiso 1 1 calc R
H(21A) H 0.7850 0.7902 1.2381 0.046 Uiso 1 1 calc R
H(21B) H 0.6274 0.8248 1.3246 0.046 Uiso 1 1 calc R
H(21C) H 0.7329 0.9492 1.2244 0.046 Uiso 1 1 calc R
H(81A) H 0.0808 1.0342 1.1282 0.043 Uiso 1 1 calc R
H(81B) H 0.2164 1.0559 1.1822 0.043 Uiso 1 1 calc R
H(81C) H 0.0887 0.9228 1.2387 0.043 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_radius_bond
F 0.72
O 0.73
N 0.75
C 0.77
H 0.32
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(9) O(1) N(2) 103.74(11)
C(105) O(106) C(107) 117.08(14)
C(3) N(2) O(1) 112.95(13)
C(3) N(2) C(21) 131.58(14)
O(1) N(2) C(21) 114.93(12)
O(3) C(3) N(2) 123.66(15)
O(3) C(3) C(4) 131.74(15)
N(2) C(3) C(4) 104.59(13)
C(9) C(4) C(5) 120.47(14)
C(9) C(4) C(3) 106.62(14)
C(5) C(4) C(3) 132.91(13)
C(4) C(5) C(6) 118.34(13)
C(5) C(6) C(7) 118.48(14)
C(5) C(6) C(10) 121.20(13)
C(7) C(6) C(10) 120.31(14)
C(8) C(7) C(6) 124.41(15)
C(7) C(8) C(9) 114.35(13)
C(7) C(8) C(81) 123.62(14)
C(9) C(8) C(81) 122.02(14)
O(1) C(9) C(4) 111.98(13)
O(1) C(9) C(8) 124.11(13)
C(4) C(9) C(8) 123.91(15)
C(101) C(10) C(6) 120.93(13)
C(101) C(10) C(11) 121.54(14)
C(6) C(10) C(11) 117.53(12)
C(16) C(11) C(12) 118.71(13)
C(16) C(11) C(10) 120.98(13)
C(12) C(11) C(10) 120.30(13)
C(13) C(12) C(11) 120.40(13)
C(12) C(13) C(14) 121.39(13)
C(12) C(13) C(131) 118.09(13)
C(14) C(13) C(131) 120.50(13)
C(15) C(14) C(13) 116.74(13)
F(15) C(15) C(16) 118.01(13)
F(15) C(15) C(14) 118.41(13)
C(16) C(15) C(14) 123.58(14)
C(15) C(16) C(11) 119.15(13)
C(10) C(101) C(102) 129.24(14)
C(101) C(102) C(103) 110.48(13)
C(104) C(103) C(102) 113.47(14)
C(105) C(104) C(103) 115.15(14)
O(105) C(105) O(106) 123.49(15)
O(105) C(105) C(104) 126.66(15)
O(106) C(105) C(104) 109.84(13)
F(131) C(131) F(133) 106.81(15)
F(131) C(131) F(132) 106.04(14)
F(133) C(131) F(132) 105.48(15)
F(131) C(131) C(13) 113.81(13)
F(133) C(131) C(13) 112.69(14)
F(132) C(131) C(13) 111.43(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F(15) C(15) 1.3569(17)
F(131) C(131) 1.3244(18)
F(132) C(131) 1.328(2)
F(133) C(131) 1.325(2)
O(1) C(9) 1.3762(18)
O(1) N(2) 1.4192(16)
O(3) C(3) 1.2366(18)
O(105) C(105) 1.2014(19)
O(106) C(105) 1.342(2)
O(106) C(107) 1.444(2)
N(2) C(3) 1.360(2)
N(2) C(21) 1.435(2)
C(3) C(4) 1.460(2)
C(4) C(9) 1.381(2)
C(4) C(5) 1.395(2)
C(5) C(6) 1.397(2)
C(6) C(7) 1.415(2)
C(6) C(10) 1.491(2)
C(7) C(8) 1.384(2)
C(8) C(9) 1.391(2)
C(8) C(81) 1.508(2)
C(10) C(101) 1.341(2)
C(10) C(11) 1.4953(19)
C(11) C(16) 1.393(2)
C(11) C(12) 1.395(2)
C(12) C(13) 1.389(2)
C(13) C(14) 1.390(2)
C(13) C(131) 1.496(2)
C(14) C(15) 1.379(2)
C(15) C(16) 1.378(2)
C(101) C(102) 1.495(2)
C(102) C(103) 1.533(2)
C(103) C(104) 1.522(2)
C(104) C(105) 1.498(2)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C(9) O(1) N(2) C(3) 3.18(15)
C(9) O(1) N(2) C(21) 175.76(12)
O(1) N(2) C(3) O(3) 176.77(13)
C(21) N(2) C(3) O(3) 5.8(3)
O(1) N(2) C(3) C(4) -3.57(15)
C(21) N(2) C(3) C(4) -174.56(16)
O(3) C(3) C(4) C(9) -177.84(15)
N(2) C(3) C(4) C(9) 2.54(15)
O(3) C(3) C(4) C(5) 2.1(3)
N(2) C(3) C(4) C(5) -177.52(15)
C(9) C(4) C(5) C(6) -0.1(2)
C(3) C(4) C(5) C(6) 179.92(14)
C(4) C(5) C(6) C(7) 1.8(2)
C(4) C(5) C(6) C(10) -177.13(13)
C(5) C(6) C(7) C(8) -2.3(2)
C(10) C(6) C(7) C(8) 176.66(13)
C(6) C(7) C(8) C(9) 0.9(2)
C(6) C(7) C(8) C(81) 179.81(14)
N(2) O(1) C(9) C(4) -1.38(15)
N(2) O(1) C(9) C(8) 179.28(13)
C(5) C(4) C(9) O(1) 179.36(12)
C(3) C(4) C(9) O(1) -0.68(16)
C(5) C(4) C(9) C(8) -1.3(2)
C(3) C(4) C(9) C(8) 178.66(13)
C(7) C(8) C(9) O(1) -179.83(13)
C(81) C(8) C(9) O(1) 1.2(2)
C(7) C(8) C(9) C(4) 0.9(2)
C(81) C(8) C(9) C(4) -178.03(14)
C(5) C(6) C(10) C(101) 151.32(15)
C(7) C(6) C(10) C(101) -27.6(2)
C(5) C(6) C(10) C(11) -28.0(2)
C(7) C(6) C(10) C(11) 153.06(13)
C(101) C(10) C(11) C(16) -53.1(2)
C(6) C(10) C(11) C(16) 126.26(16)
C(101) C(10) C(11) C(12) 125.50(17)
C(6) C(10) C(11) C(12) -55.1(2)
C(16) C(11) C(12) C(13) 2.2(2)
C(10) C(11) C(12) C(13) -176.44(15)
C(11) C(12) C(13) C(14) -1.0(3)
C(11) C(12) C(13) C(131) -179.47(16)
C(12) C(13) C(14) C(15) -0.5(2)
C(131) C(13) C(14) C(15) 177.92(16)
C(13) C(14) C(15) F(15) -178.93(14)
C(13) C(14) C(15) C(16) 0.8(3)
F(15) C(15) C(16) C(11) -179.88(14)
C(14) C(15) C(16) C(11) 0.3(3)
C(12) C(11) C(16) C(15) -1.9(2)
C(10) C(11) C(16) C(15) 176.77(15)
C(6) C(10) C(101) C(102) 178.39(15)
C(11) C(10) C(101) C(102) -2.3(3)
C(10) C(101) C(102) C(103) 121.89(17)
C(101) C(102) C(103) C(104) 170.62(13)
C(102) C(103) C(104) C(105) 82.28(17)
C(107) O(106) C(105) O(105) 1.8(2)
C(107) O(106) C(105) C(104) -177.82(14)
C(103) C(104) C(105) O(105) 2.9(2)
C(103) C(104) C(105) O(106) -177.50(13)
C(12) C(13) C(131) F(131) -164.54(15)
C(14) C(13) C(131) F(131) 17.0(2)
C(12) C(13) C(131) F(133) -42.7(2)
C(14) C(13) C(131) F(133) 138.79(17)
C(12) C(13) C(131) F(132) 75.6(2)
C(14) C(13) C(131) F(132) -102.86(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4982536
